Strychnos 1990 - 2004 - Crops for the Future

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Author Title Year Source title Reference Ban, Y. Total syntheses of the natural-products from alkaloids to terpenes 1993 Journal of Synthetic Organic Chemistry Japan 51(2): 111-127 Abstract This review describes the studies on the total syntheses of the natural products, particularly alkaloids and terpenes, which involves the determination of absolute configurations of emetine, yohimbin and reserpine. It has been attempted in principle that the synthesis should be developed by utilization of the new reactions originated in our own laboratory. The successful syntheses are demonstrated by ''one-step synthesis of beta-carboline derivatives'', ''development of a new synthetic method for 3,3- disubstituted oxindole derivatives, which method was extended to the synthesis of various indole alkaloids through a common intermediate'', ''the total synthesis of strychnos, aspidosperma and schizozygane alkaloids by photo-isomerization of 1-acylindole to 3-acylindolenine'', ''the crisscross annulation for syntheses of heterocycles and the natural products'' and ''bis (trimethylsilyl enol ether has been utilized as a 'masked acyl anion' for the synthesis of terpenses and the biologically active c y c l i c l a c t o n e s ' ' . Author Title Year Source title Reference Bennasar, M. L., E. Zulaica, J. M. Jimenez and J. Bosch Studies on the synthesis of mavacurine-type indole alkaloids - 1st total synthesis o 1993 Journal of Organic Chemistry 58(27): 7756-7767 Abstract Closure of the six-membered C ring of pentacyclic mavacurine-type alkaloids from suitably substituted tetracyclic substructures embodying rings ABDE of these alkaloids, either by electrophilic cyclization upon the indole 3-position or by intramolecular alkylation of the piperidine nitrogen, failed. In contrast, 6a-homopleiocarpamine (45) has been synthesized from dithioacetal 42 by an electrophilic cyclization involving the closure of the seven-membered C ring. The first total synthesis of the alkaloid 2,7-dihydropleiocarpamine (68) has been achieved by photocyclization of the tetracyclic chloroacetamide 54 as the key step. The required tetracyclic ABDE ring systems were prepared by a straightforward sequence consisting of nucleophilic addition of a 1-indoleacetatic ester enolate to the gamma position of a pyridinium salt, acid cyclization of the resulting 1,4- dihydropyridine, and final elaboration of the (E)-ethylidene substituent. An alternative synthesis of the tetracyclic alkaloid vinoxine (10a) is also reported.
Author Title Year Source title Reference Abstract Bonjoch, J., D. Sole and J. Bosch A new, general synthetic pathway to strychnos indole alkaloids - 1st total synthesi 1993 Journal of the American Chemical Society 115(5): 2064-2065 - Author Title Year Source title Reference Bonjoch, J., D. Sole and J. Bosch Novel general and flexible method for synthesis of Strychnos type indole alkaloid 1993 Anales De Quimica 89(1): 113-114 Abstract Starting from cis-3a-(o-nitrophenyl)octahydroindol-4-one (1), the pentacyclic Strychnos alkaloids tubifolidine and echitamidine were synthesized in nine and twelve steps, respectively, the indole nucleus being formed in the last synthetic steps by reductive cyclization of a tricyclic alpha-(on i t r o p h e n y l ) k e t o n e . Author Title Year Source title Reference Abstract Bonjoch, J., D. Sole and J. Bosch A new, general synthetic pathway to strychnos indole alkaloids. First total synthes 1993 Journal of the American Chemical Society 115(5): 2064 -
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